You have been lucky with jobs. Out of the last 5 years, my father has had the option of having insurance through his workplace for a total of 4 months. He got laid off from his job. He then spent a year on unemployment improving his skills and looking for another professional job. After giving up on that, he got the only job that he could, working as an orderly in a mental institution (which did not give him health insurance either). After several more months, he found a job but he was a contractor so again, no benefits. He spent 3 years working for the company with his manager constantly promising him that a permanent job offer was going to occur soon, once the group gets the product out. The product flopped, the group got disbanded, and all contracts terminated, so he was once again laid off. Finally, this August he found a permanent job with benefits.
One of my friends has to get insurance through her school because both her parents run a small business so to get insurance for the family would be prohibitively expensive. Her parents are uninsured since it is cheaper to just pay medical bills out of pocket.
This is the reality for I'd say...60% of Americans, especially in non-urban regions. The only reason I have health insurance is because my parents worked for the city government and I most likely will follow suit (at either the city or state level to begin with).
Urban health care is much more accessible and sometimes more affordable than rural in my opinion.
I honestly don't see how people don't get jobs.
Haha, have you looked around you? Unemployment currently approaching 10% (Assumed 20% for those other 10% dropped from unemployment benefits).
This means something close to 1 in 5 Americans are out of work 
As I've stated on numerous occasions throughout this board, I live and work in Northern Virginia so I don't really see most of the country. Government money is floating around here (thanks for your taxes) and I have
no friends or family who are currently unemployed or have been for reasons other than resignation in the past couple of years. So, looking around me doesn't do much good because I'm where the money's at.
However, what I do see around me are retail stores with job openings. I do see food joints with positions available. I do see monster.com and washingtonpost.com's job listings being added to daily. I fully understand that baby boomers are refusing to give up their positions because they either can't retire or simply don't want to. This puts a strain on generation X and a bigger one on the early Y because we went to university in DROVES compared to all previous generations. We're also the first generation to experience what is called the "Quarter Life Crisis" because of this over populated professional workforce. Kids these days get home from college and sit at home because they can't find a professional job and don't want to put a retail job on their resume as their current workplace.
This logic was sound in a stable workforce. Getting a job below your credentials wasn't something you wanted to do for your interview. However, in this workforce, it's quite the opposite. It shows an ability to do what needs to be done, regardless of the cost. We just hired a new chemist here and he stood out above the other BECAUSE he continued to work jobs that were "below" him to get bye whereas a few other candidates did not.